Ethyl 3-amino-4-hydroxybenzoate → Ethyl 2-(3-chloropropyl)-5-benzoxazolecarboxylate

HRID 1195665Notes

Reaction equation

HRID 1195665 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.[Cl:15][CH2:16][CH2:17][CH2:18][C:19](=N)OCC>ClC(Cl)Cl>[Cl:15][CH2:16][CH2:17][CH2:18][C:19]1[O:13][C:12]2[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 12208891Ethyl 3-amino-4-hydroxybenzoateHCID 13163359Ethyl 4-chlorobutanimidate hydrochloride

Product 1

HCID 54024397Ethyl 2-(3-chloropropyl)-5-benzoxazolecarboxylateYield 74.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 9 parts of ethyl 3-amino-4-hydroxybenzoate, 10.2 parts of ethyl 4-chlorobutanimidate hydrochloride and 150 parts of trichloromethane was stirred for 24 hours at 20° C. The separated organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The eluent of the desired fraction was evaporated, yielding 10 parts (74.7%) of ethyl 2-(3-chloropropyl)-5-benzoxazolecarboxylate as a residue (interm. 25).

Workup

  1. customThe separated organic layer was dried
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue was purified by column chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  6. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-6d13d5a73a284bd9be619e46b9c4caa2
Source dataset
uspto-grants-1992_05
Patent number
US05112825

Reaction notes

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